Methanol → 4-(4-Fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carboxylic acid

HRID 1676401Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1676401
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][N:11]=[C:10](C#N)[C:9]2=[O:16])=[CH:4][CH:3]=1.[OH:17]S(O)(=O)=O.[CH3:22][OH:23]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:22]([OH:17])=[O:23])[C:9]2=[O:16])=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 673472474-(4-Fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carbonitrile

Produkt 1

HCID 673494894-(4-Fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carboxylic acid

Versuchsvorschrift

A mixture of 4-(4-fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carbonitrile (0.42 g, 1.95 mmol) and H2SO4 (4.16 mL, 78.1 mmol) was stirred at room temperature for 17 hours. Then the reaction mixture (amide intermediate) was added to MeOH (50 mL), and then the reaction was heated to 70° C. for 2.5 hours. The reaction mixture (methyl ester compound) was quenched with ice-water and treated with aq. 2N NaOH solution (for hydrolysis) at 0° C. The mixture was acidified with aq. 1N HCl, extracted with EtOAc, dried over MgSO4, and concentrated to afford 0.315 g (69% for 3-step process in one pot reaction) of the desired product which was rinsed with Et2O. 1H-NMR (400 MHz, DMSO-d6) δ 7.90 (d, 1H), 7.60 (m, 2H), 7.52 (d, 1H), 7.42 (t, 2H).

Aufarbeitung

  1. temperaturethe reaction was heated to 70° C. for 2.5 hours
  2. customThe reaction mixture (methyl ester compound) was quenched with ice-water
  3. additiontreated with aq. 2N NaOH solution (for hydrolysis) at 0° C
  4. extractionextracted with EtOAc
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto afford

Quellen und Nachweise

ORD-Eintrag
ord-e60ee085bea948ec99847ad95433e725
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003662B2

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